Novel amino-indazole compounds

Abstract

This invention provides novel tertiary aminoindazole compounds of the following general formula: ##SPC1## Wherein R represents a hydrogen or halogen atom; R 1 represents an alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group; R 2 and R 3 both represent a lower alkyl or aralkyl group and W represents a branched chain alkylene group, and salts, especially acid addition and quaternary ammonium salts thereof, and processes for making them. Such compounds are pharmacologically active in that they exhibit antiinflammatory and analgesic effects so the invention also provides pharmaceutical compositions containing one or more of these compounds as the active ingredient. They are also useful anti-microbial agents.

What we claim is: 
     
       1. A tertiary amino-indazole compound of formula I: ##SPC12## wherein   R is a hydrogen atom or a halogen atom;   R 1  is an alkyl group having 1 to 6 carbon atoms, or a phenyl alkyl group, the alkyl group having 1 to 6 carbon atoms;   R 2  and R 3  which may be the same or different and each is an alkyl group having 1 to 6 carbon atoms;   W is a branched chain alkylene group comprising a divalent straight chain lower alkyl group having 1 to 6 carbon atoms pendant from the beta or gamma carbon atom relative to the carbon atom; or a non-toxic acid addition salt thereof.     
     
     
       2. A tertiary amino-indazole compound of formula I according to claim 1 wherein: R is a hydrogen atom or a chlorine atom;   R 1  is an alkyl group having 1 to 6 carbon atoms;   R 2  and R 3 , which may be the same or different, each represents a methyl group or an ethyl group; and,   W is a group of the formula: ##EQU3##   
     
     
       3. A tertiary amino-indazole compound of formula I' ##SPC13## wherein   R is a hydrogen atom or a halogen atom which is in the 5- or 6- position, or a non-toxic acid addition salt thereof.   
     
     
       4. A tertiary amino-indazole compound of formula I' according to claim 3 wherein R is a hydrogen atom or a chlorine atom. 
     
     
       5. 1-Benzyl-3-[(2-ethyl-2-dimethylamino)-ethoxy]-1H-indazole or a non-toxic acid addition salt thereof. 
     
     
       6. 1-Benzyl-3-[(2-ethyl-2-dimethylamino)-ethoxy]-1H-indazole hydrochloride. 
     
     
       7. 1-Benzyl-3-[(2-ethyl-2-dimethylamino)-ethoxy]-5-chloro-1H-indazole or a non-toxic acid addition salt thereof. 
     
     
       8. 1-Benzyl-3-[(2-ethyl-2-dimethylamino)-ethoxy]-5-chloro-1H-indazole hydrochloride.